Anna Osceola

It's a feeling of taking care of someone else and being taken care of," Hamm said of the relationship now headed for marriage.

But romance between the two did not appear to bloom until 2020, [Entertainment Weekly](https://ew.com/tv/jon-hamm-anna-osceola-engaged/) noted. [ended in 2015](https://www.latimes.com/entertainment/gossip/la-et-mg-jon-hamm-jennifer-westfeldt-split-breakup-20150908-story.html). [told Howard Stern in 2022](https://www.youtube.com/watch?v=EvnAzqEgtkA). [who flirted with Hamm’s Don Draper](https://www.latimes.com/entertainment-arts/tv/story/2023-02-27/jon-hamm-engaged-anna-osceola-mad-men-confess-fletch) in the series finale. [confirmed the news](https://people.com/movies/jon-hamm-and-anna-osceola-are-engaged/) on Monday. [Mad Men](https://www.huffpost.com/entertainment/topic/mad-men)” co-stars [Jon Hamm](https://www.huffpost.com/entertainment/topic/jon-hamm) and Anna Osceola have made a longer-term commitment: They’re reportedly engaged!

Jon Hamm and Anna Osceola are reportedly set to tie the knot after two years of dating. According to People, Hamm, 51, recently popped the question after ...

Doing so has “made the relationship that i’m in now even more meaningful and opened up the possibility of things like being married, having kids, you know defining a new version of happiness, life, wellness,” the actor revealed. “All that stuff that sounds hokey and whatever but it’s real and, for one of a better word, it’s what I’m working for. [People](https://people.com/movies/jon-hamm-and-anna-osceola-are-engaged/), Hamm, 51, recently popped the question after first meeting Osceola, 34, on the set of “Mad Men” back in 2015.

"Mad Men" star Jon Hamm is reportedly engaged to his "Confess, Fletch" co-star Anna Osceola. People reported Monday that the actors got engaged after two ...

Actor Jon Hamm (51) is reportedly engaged to his longtime girlfriend, actress Anna Osceola (34). Both Hamm and Osceola are known for being very private, ...

The big eyebrow-raising issue here is the fact that Jon Hamm is finally seeming to step into the arena of marriage. Hamm and Osceola made their relationship official in public in March 2022 at an Oscars afterparty and stepped out for numerous public events that year, including the ESPY Awards and a screening of Hamm's film Confess, Fletch, which Osceola also made an appearance in. Both Hamm and Osceola are known for being very private, keeping their respective lives off of social media; however, [PEOPLE](https://people.com/movies/jon-hamm-and-anna-osceola-are-engaged/) has confirmed through its sources that Hamm did pop the question to Osceola.

Anna Osceola reportedly said yes to beau Jon Hamm!The Morning Show star and the Confess actor are engaged after dating for two years as per a report by ...

"That's made the relationship that I'm in now even more meaningful and opened up the possibility of things like being married, having kids, defining a new version of happiness, life, wellness," he added. "I'm in a relationship right now and it's comfortable. "And it’s also been a process of working on myself, my mental health and unpacking all of that trauma, my realizing that, you know, when you lose somebody that's so important to you like a mother so early, that creates a wound that blocks a lot of that emotional accessibility, that blocks a lot of that availability, and vulnerability."

It's a feeling of taking care of someone else and being taken care of," Hamm said of the relationship now headed for marriage.

Anna Osceola and Jon Hamm began their romance two years ago and have taken their relationship to the next level as they get engaged.

There, he revealed that he could see himself marrying and having kids someday. After dating for two years, Anna Osceola and Jon Hamm decided to take things up a notch. The actors made their red carpet debut at an Oscars afterparty in March 2022. They also took a vacation to Italy together in September 2021. The Mad Men co-stars, who also happen to be Confess, Fletch co-stars, started dating in 2020. Fans woke up to the news of Anna and Jon getting engaged following a private relationship.

Jon Hamm and his new fiancee Anna Osceola looked smitten as they headed out for dinner in LA recently - days before their engagement was announced.

Fletcher - which was originally played by Chevy Chase in the 1985 and 1989 films. I don't have that paragon of married life to look at and think, 'Oh yeah, that's it! I'm in a relationship right now and it's comfortable.' That's what I want!'' I'm not judging it one way or another. 'This is all part of what I'm saying,' Jon said at the time.

Since meeting on the set of 'Mad Men,' Jon Hamm and Anna Osceola went from costars to romantic partners — relive their sweetest moments.

[Jennifer Westfeldt](https://www.usmagazine.com/celebrities/jennifer-westfeldt/). [Howard Stern](https://www.usmagazine.com/celebrities/howard-stern/), “It’s a feeling of taking care of someone else and being taken care of. Though briefly linked in 2017, [Us Weekly](https://www.usmagazine.com/celebrity-news/news/jon-hamm-is-dating-former-mad-men-costar-anna-osceola/) confirmed the couple’s romance in June 2020. A source told [Us](https://www.usmagazine.com/celebrity-news/news/jon-hamm-jennifer-westfeldt-why-they-split-201599/) at the time that although the two “definitely tried” to make things work, there was “always a rift” between them, noting, “He wanted kids and she didn’t.” “It’s fine,” he said, adding, “It’s hard. [series finale of the AMC drama](https://www.usmagazine.com/entertainment/news/mad-men-series-finale-recap-don-drapers-fate-revealed-2015185/) in 2015, as Osceola played Clementine, a receptionist at the retreat Hamm’s character attended. All that stuff, it sounds hokey and whatever, but it’s real.” It’s really hard. Though neither are on social media, they have shared several fun moments over the years, from red carpet appearances to European vacations to sharing the screen again and more. [InStyle](https://www.instyle.com/celebrity/jon-hamm-man-of-style). [Us](https://www.usmagazine.com/celebrity-news/news/mad-men-costars-jon-hamm-and-anna-osceola-are-engaged/) in February 2023. [Jon Hamm](https://www.usmagazine.com/celebrities/jon-hamm/) win an Emmy for his role as Don Draper on [Mad Men](https://www.usmagazine.com/shows/mad-men/), but the show introduced him to the love of his life, [Anna Osceola](https://www.usmagazine.com/celebrity-news/news/jon-hamm-is-very-much-in-love-with-girlfriend-anna-osceola/).

Jon Hamm's new fiancee Anna Osceola cut a casual figure as she went on a dog walk in Los Angeles on Tuesday - one day after the pair's engagement was ...

I don't have that paragon of married life to look at and think, "Oh yeah, that's it! That said, I'm in a committed relationship, and if it ever came up, I'm not ruling it out.' That's what I want!" The Emmy Award winner got candid when he said he has been seeking therapy in recent years and has found that a lot of his trauma comes from losing his mother to colon cancer when he was just ten-years-old. I'm not judging it one way or another. The statements stand in stark contrast to comments he made in 2012, in which he revealed he didn't believe in marriage and that he had no yearning to be a father.